1,3-Dibromopropane → 2-(3-Bromopropoxy)-1H-isoindole-1,3(2H)-dione

HRID 868548Notes

Reaction equation

HRID 868548 reaction equation
[OH:1][N:2]1[C:6](=[O:7])[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]2[C:3]1=[O:12].[Br:13][CH2:14][CH2:15][CH2:16]Br.C(N(C(C)C)CC)(C)C>CC#N>[Br:13][CH2:14][CH2:15][CH2:16][O:1][N:2]1[C:3](=[O:12])[C:4]2=[CH:11][CH:10]=[CH:9][CH:8]=[C:5]2[C:6]1=[O:7]

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 10665N-HydroxyphthalimideHCID 81531Diisopropylethylamine

Product 1

HCID 2655692-(3-Bromopropoxy)-1H-isoindole-1,3(2H)-dione

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of N-hydroxyphthalimide (2.0 g) and 1,3-dibromopropane (2.49 ml) in 50 ml of dry CH3CN was added diisopropylethylamine (4.27 ml). The mixture was stirred at room temperature. After 4 hours the volatiles were removed in vacuo. The residue was triturated with Et2O to provide 2.53 g of while solid, homogeneous by TLC.

Workup

  1. customAfter 4 hours the volatiles were removed in vacuo
  2. customThe residue was triturated with Et2O
  3. customto provide 2.53 g of while solid

Sources & evidence

ORD record
ord-5a566a0ee464489bbbda7849ac50b7d0
Source dataset
uspto-grants-1988_10
Patent number
US04780466

Reaction notes

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